Patent GB-989627-A (GB)
Title: New triazolidines and process for preparing them
IPC: C07D271/113
Filed: 1961-07-20
Abstract: The invention comprises compounds of the general formula <FORM:0989627/C2/1> and their salts with inorganic or organic bases in which R represents an aryl group, wherein 1 or 2 hydrogen atoms may be substituted by halogen atoms, or alkyl or alkoxy groups of 1-4 carbon atoms, R1 represents a halogen atom, an alkyl or alkoxy group of 1-4 carbon atoms, an aryloxy group, an aralkoxy group the alkyl component of which contains 1-4 carbon atoms, R2 represents a halogen atom, a trifluoromethyl group, an alkyl, alkoxy, or alkylmercapto group of 1-8 carbon atoms, a cycloalkyl group of 5-6 carbon atoms, a benzhydryl group, an aryl group, an aralkyl or aralkoxy group the alkyl component of which contains 1-4 carbon atoms, an aryloxy or arylmercapto group or an aliphatic monocarboxy acyl group, R3 represents a halogen atom, a trifluoromethyl group, an alkyl or alkoxy group of 1-4 carbon atoms, a nitro group, an aliphatic monocarboxy acyl group containing 5-6 carbon atoms, a cyclo-aliphatic-monocarboxy acyl group containing 5-6 carbon atoms, an araliphatic monocarboxy acyl group the alkyl component of which contains 1-4 carbon atoms, an aromatic monocarboxy acyl group, an alkyl- or alkenylsulphonyl group containing up to 4 carbon atoms or an arylsulphonyl group, R4 represents an alkyl or alkoxy group of 1-4 carbon atoms, R5 represents an alkyl- or alkoxy group of 1-4 carbon atoms or a cycloalkyl group of 5 or 6 carbon atoms and in which formula three of the substituents R2, R3, R4 and R5 may also represent hydrogen and in which alkyl, alkylene or aryl groups that may be present in R1-R5 may, if desired, be substituted by a hydroxy group, an alkoxy group of 1-4 carbon atoms or by a halogen atom, and two adjacent residues may be members of a methylene dioxy or a benzofuran ring; the preparation thereof by methods known for the preparation of triazolides, i.e. (a) by reacting semicarbazide acids of the general formulae <FORM:0989627/C2/2> or their esters with alkaline agents or by heating them in the absence of alkaline agents, or (b) by reacting semicarbazides of the formulae <FORM:0989627/C2/3> with derivatives of carbonic acid, e.g. phosgene, or (c) by reacting derivatives of phenylhydrazine-N1,N2-dicarboxylic acids of the formula <FORM:0989627/C2/4> e.g. esters, amides, or halides, with amines of the general formula <FORM:0989627/C2/5> or (d) by reacting reactive derivatives of phenyl hydrazine -N1- or -N2- monocarboxylic acids of the formulae <FORM:0989627/C2/6> e.g. esters, amides or halides, with reactive N-carboxylic acid derivatives of amines of the above formula, e.g. phenyl ureas, phenylcarbamic acid esters, or acid halides or phenylisocyanates, or (e) by reacting phenylhydrazines R.NHNH2 with amines of the above formula in the presence of reactive derivatives of carbonic acid, e.g. urea, or (f) by replacing the sulphur atom in thiotriazolidines of the formula <FORM:0989627/C2/7> by an oxygen atom, e.g. by oxidation, or (g) by reacting thiotriazolidines of the general formula <FORM:0989627/C2/8> with an amine of the above formula, or (h) by heating oxadiazolone derivatives of the general formula <FORM:0989627/C2/9> with an amine of the above formula, or (i) by reacting phenyl hydrazines of the formula R.NHNH2 with reactive derivatives of aniline-N,N-dicarboxyli acids of the formula <F\10> e.g. esters with lower alcohols, or phenols, amide esters and diamides, and, if desired, forming a salt of the product with an organic or inorganic base.  5 - Ethoxy - 3 - phenyl - 1,3,4 - oxadiazolone - (2) was prepared from ammonia and phenylhydrazine-b -carboxylic acid ethyl ester-a -carboxylic acid chloride.  1 - Phenyl - 4 - (2,4,6 - trimethylphenyl) - 3 - oxo - 5 - thio - 1,2,4 - triazolidine is prepared from phenylhydrazine-b -carboxylic acid-ethyl-ester-a -thiocarboxylic acid chloride and mesidine.  Pharmaceutical compositions suitable for oral or parenteral administration in lowering of blood pressure comprises a compound of the invention and a pharmaceutically acceptable carrier. The compositions may be in the form of tablets or dragees or solutions for injection.  The compositions also exhibit antiphlogistic, analgesic and vasodilatory action (on coronary vessels).